JP5548614B2 - アルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、それらの製造方法及び使用 - Google Patents
アルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、それらの製造方法及び使用 Download PDFInfo
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- JP5548614B2 JP5548614B2 JP2010515387A JP2010515387A JP5548614B2 JP 5548614 B2 JP5548614 B2 JP 5548614B2 JP 2010515387 A JP2010515387 A JP 2010515387A JP 2010515387 A JP2010515387 A JP 2010515387A JP 5548614 B2 JP5548614 B2 JP 5548614B2
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- Prior art keywords
- alkyl
- salt
- bis
- acid
- palladium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Alkyl phosphonous acid Chemical compound 0.000 title claims description 293
- 238000000034 method Methods 0.000 title claims description 50
- 230000008569 process Effects 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title description 21
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 88
- 239000003054 catalyst Substances 0.000 claims description 66
- 150000001336 alkenes Chemical class 0.000 claims description 57
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 53
- 239000003063 flame retardant Substances 0.000 claims description 40
- 239000005977 Ethylene Substances 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 39
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 35
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 34
- 229910052723 transition metal Inorganic materials 0.000 claims description 33
- 150000003624 transition metals Chemical class 0.000 claims description 32
- 229910052751 metal Inorganic materials 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 24
- 239000003446 ligand Substances 0.000 claims description 23
- 150000003623 transition metal compounds Chemical class 0.000 claims description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 21
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002602 lanthanoids Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000011814 protection agent Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000009970 fire resistant effect Effects 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 229920000642 polymer Polymers 0.000 description 64
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000002904 solvent Substances 0.000 description 35
- 239000000047 product Substances 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 229920001577 copolymer Polymers 0.000 description 32
- 229920001169 thermoplastic Polymers 0.000 description 32
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- 239000012071 phase Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 17
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000012778 molding material Substances 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
- 229920001228 polyisocyanate Polymers 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- 229920001187 thermosetting polymer Polymers 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000008139 complexing agent Substances 0.000 description 10
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 150000003003 phosphines Chemical class 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- 229920001707 polybutylene terephthalate Polymers 0.000 description 8
- 239000004416 thermosoftening plastic Substances 0.000 description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- 239000005062 Polybutadiene Substances 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000004634 thermosetting polymer Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 229920001684 low density polyethylene Polymers 0.000 description 6
- 239000004702 low-density polyethylene Substances 0.000 description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 229920002943 EPDM rubber Polymers 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 229920005594 polymer fiber Polymers 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 229920006055 Durethan® Polymers 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910000990 Ni alloy Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- AQBOUNVXZQRXNP-UHFFFAOYSA-L azane;dichloropalladium Chemical compound N.N.N.N.Cl[Pd]Cl AQBOUNVXZQRXNP-UHFFFAOYSA-L 0.000 description 4
- NOWPEMKUZKNSGG-UHFFFAOYSA-N azane;platinum(2+) Chemical compound N.N.N.N.[Pt+2] NOWPEMKUZKNSGG-UHFFFAOYSA-N 0.000 description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229920001903 high density polyethylene Polymers 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 229920000092 linear low density polyethylene Polymers 0.000 description 4
- 239000004707 linear low-density polyethylene Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- NYBDEQVBEYXMHK-UHFFFAOYSA-N methyl prop-2-enoate;5-phenylpenta-2,4-dienenitrile Chemical compound COC(=O)C=C.N#CC=CC=CC1=CC=CC=C1 NYBDEQVBEYXMHK-UHFFFAOYSA-N 0.000 description 1
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- RYOPVFUGUFDYKP-UHFFFAOYSA-L n,n-dimethyl-1-phenylmethanamine;palladium(2+);dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.CN(C)CC1=CC=CC=[C-]1.CN(C)CC1=CC=CC=[C-]1 RYOPVFUGUFDYKP-UHFFFAOYSA-L 0.000 description 1
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- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
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- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- VXIWVFJYLFAWKN-UHFFFAOYSA-J tetrasodium 3-[[2-[2-[bis(3-sulfonatophenyl)phosphanylmethyl]phenyl]phenyl]methyl-(3-sulfonatophenyl)phosphanyl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(CC=2C(=CC=CC=2)C=2C(=CC=CC=2)CP(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 VXIWVFJYLFAWKN-UHFFFAOYSA-J 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940006280 thiosulfate ion Drugs 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical compound Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical group N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- MOSFSEPBWRXKJZ-UHFFFAOYSA-N tridecylphosphane Chemical compound CCCCCCCCCCCCCP MOSFSEPBWRXKJZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- OUNAJLWMVZKFDK-UHFFFAOYSA-K tripotassium 2-bis(2-sulfonatophenyl)phosphanylbenzenesulfonate Chemical compound [K+].[K+].[K+].[O-]S(=O)(=O)C1=CC=CC=C1P(C=1C(=CC=CC=1)S([O-])(=O)=O)C1=CC=CC=C1S([O-])(=O)=O OUNAJLWMVZKFDK-UHFFFAOYSA-K 0.000 description 1
- PBZIEJBOAYSADZ-UHFFFAOYSA-K tripotassium 5-bis(2,4-dimethyl-5-sulfonatophenyl)phosphanyl-2,4-dimethylbenzenesulfonate Chemical compound [K+].[K+].[K+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1P(C=1C(=CC(C)=C(C=1)S([O-])(=O)=O)C)C1=CC(S([O-])(=O)=O)=C(C)C=C1C PBZIEJBOAYSADZ-UHFFFAOYSA-K 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
- IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- RTNPUWLBWXIECX-UHFFFAOYSA-N tris[4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)phenyl]phosphane Chemical compound C1=CC(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=CC=C1P(C=1C=CC(=CC=1)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C1=CC=C(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=C1 RTNPUWLBWXIECX-UHFFFAOYSA-N 0.000 description 1
- CTSUHMKFLNRDPS-UHFFFAOYSA-K trisodium;2-bis(2-sulfonatophenyl)phosphanylbenzenesulfonate Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC=C1P(C=1C(=CC=CC=1)S([O-])(=O)=O)C1=CC=CC=C1S([O-])(=O)=O CTSUHMKFLNRDPS-UHFFFAOYSA-K 0.000 description 1
- YVYHEZNITVEWDK-UHFFFAOYSA-K trisodium;5-bis(2,4-dimethyl-5-sulfonatophenyl)phosphanyl-2,4-dimethylbenzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1P(C=1C(=CC(C)=C(C=1)S([O-])(=O)=O)C)C1=CC(S([O-])(=O)=O)=C(C)C=C1C YVYHEZNITVEWDK-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical group C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4866—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the ester moiety containing a substituent or structure which is considered as characteristic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/485—Polyphosphonous acids or derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007032669.8 | 2007-07-13 | ||
| DE102007032669A DE102007032669A1 (de) | 2007-07-13 | 2007-07-13 | Alkylphosphonigsäuren, -salze und -ester, Verfahren zu deren Herstellung und ihre Verwendung |
| PCT/EP2008/005382 WO2009010188A2 (de) | 2007-07-13 | 2008-07-02 | Alkylphosphonigsäuren, -salze und -ester, verfahren zu deren herstellung und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010533133A JP2010533133A (ja) | 2010-10-21 |
| JP5548614B2 true JP5548614B2 (ja) | 2014-07-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2010515387A Expired - Fee Related JP5548614B2 (ja) | 2007-07-13 | 2008-07-02 | アルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、それらの製造方法及び使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8293938B2 (es) |
| EP (1) | EP2178891B8 (es) |
| JP (1) | JP5548614B2 (es) |
| KR (1) | KR101564917B1 (es) |
| CN (1) | CN101720329B (es) |
| DE (1) | DE102007032669A1 (es) |
| ES (1) | ES2446297T3 (es) |
| WO (1) | WO2009010188A2 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008063627A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monohydroxyfunktionalisierten Dialkylphosphinsäuren,-estern und -salzen mittels Ethylenoxid und ihre Verwendung |
| DE102010018684A1 (de) * | 2010-04-29 | 2011-11-03 | Clariant International Ltd. | Verfahren zur Herstellung von Mischungen aus Alkylphosphonigsäuresalzen und Dialkylphosphinsäuresalzen |
| DE102010018682A1 (de) * | 2010-04-29 | 2011-11-03 | Clariant International Ltd. | Verfahren zur Herstellung von Alkylphosphonigsäuresalzen |
| DE102011121504A1 (de) | 2011-12-16 | 2013-06-20 | Clariant International Ltd. | Gemische von Diphosphinsäuren und Alkylphosphonsäuren, ein Verfahren zu deren Herstellung und ihre Verwendung |
| DE102011121590A1 (de) * | 2011-12-16 | 2013-06-20 | Clariant International Ltd. | Gemische von Diphosphinsäuren und Alkylphosphinsäuren, ein Verfahren zu deren Herstellung und ihre Verwendung |
| DE102011121591A1 (de) | 2011-12-16 | 2013-06-20 | Clariant International Ltd. | Gemische aus Dialkylphosphinsäuren und Alkylphosphonsäuren, ein Verfahren zu deren Herstellung und ihre Verwendung |
| DE102011121503A1 (de) * | 2011-12-16 | 2013-06-20 | Clariant International Ltd. | Gemische von Dioshinsäuren und Dialkylphosphinsäuren, ein Verfahren zu deren Herstellung und ihre Verwendung |
| DE102011121900A1 (de) | 2011-12-21 | 2013-06-27 | Clariant International Ltd. | Gemische von mindestens einer Dialkylphosphinsäure mit mindestens einer anderen, davon unterschiedlichen Dialkylphosphinsäure, Verfahren zu deren Herstellung und ihre Verwendung |
| TWI447154B (zh) | 2012-11-27 | 2014-08-01 | Ind Tech Res Inst | 聚氯乙烯製品與其表面處理方法 |
| FR3002943B1 (fr) * | 2013-03-11 | 2015-03-27 | Arkema France | Sirop (meth)acrylique liquide d'impregnation d'un substrat fibreux, procede d'impregnation d'un substrat fibreux, materiau composite obtenu apres polymerisation dudit substrat pre-impregne. |
| JP6736466B2 (ja) * | 2014-08-12 | 2020-08-05 | 大塚化学株式会社 | 環状ホスホン酸ナトリウム塩の結晶及びその製造方法 |
| CN104926865A (zh) * | 2015-06-24 | 2015-09-23 | 南通泰通化学科技有限公司 | 2-羧乙基次磷酸的生产工艺 |
| CN105220552B (zh) * | 2015-09-09 | 2017-03-29 | 郑州轻工业学院 | 利用咪唑类非对称Gemini离子液体提取纤维素的方法 |
| CN107324125B (zh) * | 2017-08-14 | 2020-06-12 | 江苏金佰纳建筑装配有限公司 | 一种建筑电缆放线架 |
| CN110783586B (zh) * | 2019-11-21 | 2021-10-08 | 华南师范大学 | 一种高功率密度一次电池电解液及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2957931A (en) * | 1949-07-28 | 1960-10-25 | Socony Mobil Oil Co Inc | Synthesis of compounds having a carbonphosphorus linkage |
| DE2100779A1 (de) * | 1971-01-08 | 1972-07-20 | Farbwerke Hoechst AG vormals Meister Lucius & Brüning, 6000 Frankfurt | Verfahren zur Herstellung von Dialkylphosphinsäureestern |
| US3914345A (en) * | 1971-01-08 | 1975-10-21 | Hoechst Ag | Process for the manufacture of dialkyl-phosphinic acid esters |
| US4088678A (en) * | 1976-07-01 | 1978-05-09 | Nalco Chemical Company | Substituted succinic acid compounds and their use as chelants |
| JPS573852A (en) * | 1980-06-09 | 1982-01-09 | Mitsubishi Gas Chem Co Inc | Stabilized polyphenylene ether resin composition |
| EP0038778A3 (de) * | 1980-04-21 | 1981-11-25 | Ciba-Geigy Ag | Alkylphosphonite, Verfahren zu deren Herstellung sowie die Verwendung von Alkylphosphoniten als Fungizide |
| US5457095A (en) * | 1984-10-12 | 1995-10-10 | Ciba-Geigy Corporation | Substituted propane-phosponous acid compounds |
| US5051413A (en) * | 1986-02-13 | 1991-09-24 | Ciba-Geigy Corporation | Unsaturated amino acids |
| ATE70535T1 (de) | 1986-02-13 | 1992-01-15 | Ciba Geigy Ag | Ungesaettigte aminosaeuren. |
| US5175344A (en) * | 1986-02-13 | 1992-12-29 | Ciba-Geigy Corporation | Unsaturated amino acids |
| US4740332A (en) * | 1986-05-12 | 1988-04-26 | E. R. Squibb & Sons, Inc. | Process for preparing phosphonous acids |
| DE4220566A1 (de) * | 1992-06-24 | 1994-01-20 | Hoechst Ag | Inhibitoren retroviraler Proteasen |
| DE19604195C1 (de) * | 1996-02-06 | 1997-04-17 | Hoechst Ag | Verfahren zur Herstellung von Phosphonigsäuremonoalkylestern |
| DE19608006A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Salze von phosphonigen Säuren und deren Verwendung als Flammschutzmittel in Kunststoffen |
| BR9815058A (pt) * | 1997-11-28 | 2000-10-03 | Clariant Gmbh | Processo para a preparação de ácidos dialquilfosfìnicos |
| DE19851768C2 (de) * | 1997-11-28 | 2000-03-23 | Clariant Gmbh | Verfahren zur Herstellung von Dialkylphosphinsäuresalzen |
| DE19828863C1 (de) * | 1998-06-29 | 1999-09-02 | Clariant Gmbh | Verfahren zur Herstellung von Phosphinsäureestern und deren Verwendung |
| DE19828861C1 (de) * | 1998-06-29 | 1999-12-02 | Clariant Gmbh | Verfahren zur Herstellung von Phosphonigsäureestern und deren Verwendung |
| DE19923743C2 (de) * | 1999-05-25 | 2002-03-07 | Clariant Gmbh | Verfahren zur Herstellung von (Metall)salzen von Alkylphosphonigen Säuren II |
| DE19923615C1 (de) * | 1999-05-25 | 2000-12-14 | Clariant Gmbh | Verfahren zur Herstellung von Alkylphosphonigsäureestern |
| DE19923617C2 (de) * | 1999-05-25 | 2001-10-31 | Clariant Gmbh | Verfahren zur Herstellung von Phosphinsäureestern |
| DE19923830C1 (de) * | 1999-05-25 | 2001-02-01 | Clariant Gmbh | Verfahren zur Herstellung von Metallsalzen von Alkylphosphonigen Säuren I |
| WO2001019837A1 (en) * | 1999-09-16 | 2001-03-22 | Lupin Laboratories Limited | An improved regiospecific synthesis of phosphonous acids |
| JP2004075650A (ja) * | 2002-08-22 | 2004-03-11 | National Institute Of Advanced Industrial & Technology | アルケニルリン化合物及びその製造方法 |
| US7285587B2 (en) * | 2002-12-20 | 2007-10-23 | Eastman Chemical Company | Flame retardant polyester compositions for calendering |
-
2007
- 2007-07-13 DE DE102007032669A patent/DE102007032669A1/de not_active Withdrawn
-
2008
- 2008-07-02 US US12/668,814 patent/US8293938B2/en active Active
- 2008-07-02 WO PCT/EP2008/005382 patent/WO2009010188A2/de active Application Filing
- 2008-07-02 KR KR1020107003051A patent/KR101564917B1/ko active IP Right Grant
- 2008-07-02 ES ES08773803.5T patent/ES2446297T3/es active Active
- 2008-07-02 JP JP2010515387A patent/JP5548614B2/ja not_active Expired - Fee Related
- 2008-07-02 EP EP08773803.5A patent/EP2178891B8/de not_active Not-in-force
- 2008-07-02 CN CN200880022620.8A patent/CN101720329B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2178891B8 (de) | 2014-02-19 |
| KR101564917B1 (ko) | 2015-11-02 |
| CN101720329A (zh) | 2010-06-02 |
| EP2178891B1 (de) | 2013-12-11 |
| US20100190901A1 (en) | 2010-07-29 |
| DE102007032669A1 (de) | 2009-01-15 |
| KR20100043221A (ko) | 2010-04-28 |
| JP2010533133A (ja) | 2010-10-21 |
| CN101720329B (zh) | 2014-08-06 |
| EP2178891A2 (de) | 2010-04-28 |
| US8293938B2 (en) | 2012-10-23 |
| WO2009010188A2 (de) | 2009-01-22 |
| ES2446297T3 (es) | 2014-03-07 |
| WO2009010188A3 (de) | 2009-11-26 |
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